Baseball’s managerial fraternity will receive an infusion of new talent on Thursday when the regular season officially begins. Of the six new skippers in the sport, five will be navigating the rigors of the job for the first time in the major leagues.

Four will do so in some of the country’s most demanding media markets: Gabe Kapler in Philadelphia, Alex Cora in Boston and Mickey Callaway (Mets) along with Aaron Boone (Yankees) in New York. In Washington, Dave Martinez takes over the Nationals, a franchise that is hungry for what has been elusive success in the postseason.

All will face pressure.

As the season approached, The Athletic reached out to a collection of current and former managers in hopes of understanding the challenges that await this crop of first-time skippers.

Our 18-man panel has managed exactly 25,000 games in the major leagues, accounting for more than 154 seasons worth of experience. Collectively, they have won 20 pennants...